Man to Woman

by Jane Futa

  I knew it would be a strange and difficult transition, but I was excited to start the fall semester as Nicole. I’d never felt better in my body or happier with my life. And it wouldn’t hurt to be surrounded by a bunch of hot college guys that I could seduce.

  “I want to tell you something,” said Brianna a week before the semester started. We were sitting cross-legged and facing each other on her bedroom floor. We really had become best friends through the summer. “I wanted it to be a surprise, but I’ll be joining you at college this year.”

  “Really? That would be amazing!” I reached over and hugged her close to me. I couldn’t believe my sister and new best friend was going to be on campus with me.

  “Well, you know. I have to make sure you’re safe and all that.”

  “I’ll be fine,” I assured her.

  “Besides,” she continued, “we can go cruising for guys together.” I laughed and took her hands in mine.

  “Thanks for everything, Brianna. You’re the best sister anyone could ask for.”

  “You’re welcome, Nicole.” I smiled and we hugged again. I couldn’t believe how much had changed since I got hired at my favorite restaurant. I remembered the first time I put on Brianna’s yellow panties and stuck a hairbrush up my ass.

  My life is pretty fucking great, I thought. I can’t wait to make it great for all the future guys I meet.

  Dressed for the Interview

  Chapter 1

  I was a damn good programmer with a solid five years under my belt already. I lived in the heart of Silicon Valley where there was exponential growth as well as high turnover in a lot of respects. It was an exciting place and often just as much a devastating one.

  I’d recently been laid off to no fault of my own. The company I worked for went out of business, and that was that. To most people, getting another job should seem easy, but the competition had gotten pretty fierce. It was especially bad if you wanted better job security in one of the top companies. There were tons of startups and small companies I could’ve gotten in on, but the rent in California has never been cheap, and Silicon Valley’s allure and growth made it that much more expensive.

  I was already commuting an hour to work at my last job, just so that I could live somewhere I could afford. It was mostly worth it, though. I lived an hour from the beach, a few hours from San Francisco, and my job impressed most of my friends and family.

  To be able to afford to live in the middle of the Silicon Valley hub, however, I needed to get in with one of the most competitive companies in the area. I knew it would be a challenge, but I had no idea that my gender would end up working against me.

  I could hardly get an interview, much less a job offer. They all wanted more diversity, and I was a young, white male. Women were hard to come by in Silicon Valley, especially in programming positions.

  “I’m half tempted to apply with a woman’s name. Just to see if I finally get an interview,” I told my new roommate, Jason. We were meeting in our local coffee shop. We’d both been laid off from the same company and were struggling to pay our rent.

  “That would only upset you more,” he said. “It’s not like you’d be able to actually interview with them as a woman.”

  “Pfft, yeah. It’s almost a shame that I couldn’t just be born with a pussy.”

  Jason laughed. “Try not to get to down about it, Brent. Something will come up. There’s always something smaller in the short term. You don’t have to get in at Choodle,” he said.

  Choodle was the top search engine in the world. Their salaries were high and their job was security was all but a guarantee. I knew if I could get a spot with them I’d never have to go through getting laid off again. Or at least, it would be highly unlikely.

  When Jason and I returned home, the idea of applying as a woman was nagging me. I just had to know how much easier it’d be. Of course, he was right. It would only upset me more if they called back quickly. Still, I couldn’t sleep that night until I sent off a resume to Choodle. I sent off a resume with the name, Bella.

  I’d always liked the name Bella and figured if I had a daughter I’d name her that. I filled out the remaining application, attached the resume, and finally laid down to sleep. I slept like a rock the whole night. I knew if I hadn’t taken care of that first, though, I’d be tossing and turning for hours.

  The next morning, my phone was ringing. The screen displayed a new number. In my groggy state, I answered.

  “Yeah?”

  “Oh,” said the voice, obviously surprised. “I’m looking for a Bella White.”

  “Who?”

  “Maybe I have the wrong number. I’m calling from Choodle. We just received an application for one of our programming positions and were hoping to set up an interview. Sorry to bother you.”

  My head was spinning. “Oh! Wait! Sorry…you meant Bell-bell,” I said, desperate to cover my tracks. “She’s my sister. One second.”

  I pretended to call Bella to the phone and then I raised my voice to as high of a tone as possible. “Hello?”

  The Choodle representative explained that they were very eager to sit down with me and discuss my qualifications. I couldn’t believe what I was hearing. They must’ve seen the application and immediately called me. They couldn’t have had it in their hands longer than a few hours. My blood started to boil as much as my heart was racing.

  “So does Tuesday at 10 a.m. work for you, Ms. White?”

  I hesitated a moment. I couldn’t really set up an interview as a woman, could I? I needed more time to weight my options. I decided to agree and then cancel later.

  “Uh, yes! That’s perfect,” I said in a rush.

  “Great, Bella. The Choodle team is looking forward to meeting with you.”

  I thanked her for the call and hung up. Then I rushed into Jason’s room and shook him awake.

  “Dude, what’s your fucking problem?”

  “You’ll never believe what just happened.” He sat up quickly and rubbed his eyes. When I had his full attention, I elaborated on my insane morning.

  “You’re kidding,” he said after I explained everything.

  “Not at all. I have an interview Tuesday morning.”

  “Fuck,” he said. “You can’t really go, of course. But how can you afford to pass it up?”

  “That’s my dilemma,” I said. “What do I do?”

  “Well, if you show up as you, they’re going to be pissed. It could ruin any chances you have of ever working with them.”

  My eyes fell into a daze as my mind circled around the sudden influx of thoughts. “Yeah, true.”

  “But if you don’t go at all, you’ll miss a great opportunity.”

  “It’s not really my opportunity, though,” I told him.

  “Why not? It’s as much yours as a woman’s. You’re obviously qualified or they wouldn’t have called you. There’s only one thing you can do.”

  My eyes darted to his. His face was puffy and red from heavy sleep. “What did you have in mind?”

  “Well…how do you feel about wearing a pencil skirt?”

  Chapter 2

  “You mean…crossdress?” I couldn’t believe my ears. Was Jason really suggesting I pretend to be a woman? It was a good job, but was it worth switching genders? After all, I couldn’t just be a woman for the interview. I’d have to be a woman my entire career there.

  “And what if I actually got the job? Hm? What then?”

  “Fuck, man. I don’t know,” he said, rubbing the back of his neck. “Let’s say you go to the interview and learn a little something about what they’re looking for. Maybe that could help you land the job as a dude.”

  “We know what they’re looking for. You said it yourself. They just want me to have a pussy. For fuck’s sake. Isn’t this reverse sexism or something?”

  He shrugged. “I don’t really think we’re the ones that can make that call.”

  I sat on the edge of Jason’s bed, trying to weigh my options. “Fuck. I
don’t know the first thing about being a woman.”

  “I don’t know. You’ve always seemed a little feminine to me.” He smiled and stuck out his tongue playfully. I punched him in the arm to show him just how manly I could be. But deep down, I knew he was right. I was slender with soft features. I may have never worn a dress, but I had the body for one. “I think I know someone who could help you out.”

  “Really? Who?”

  “My little sister. She’s only 18 and is obsessed with the beauty and fashion communities on social media. She could probably make you look like an alien if you wanted.” He reached for his phone and started to dial.

  “I don’t know man. An 18 year old girl helping me switch genders? Seems kind of weird…”

  “Oh it is. But you got yourself into this mess and I kind of want to see how it all plays out.” He was laughing at me again. He brought his phone to his ear and I heard a young girl’s voice answer.

  “Hey Nina. I need you to do me a favor. No, no, you’ll like this one, I promise.”

  I left the room while he explained the details to Nina. He finally came out to tell me she had agreed. She was so excited, apparently, that she was coming over right after school. I cringed when he said the word school.

  Everything about this is so fucking wrong, I thought. But my curiosity trumped my sense of morality. I had to get into that interview.

  Nina came over hours later, despite Jason having to go out for an interview of his own. I felt a little uncomfortable being alone with an 18 year old girl, but I just kept reminding myself she was an adult, and nothing here was sexual anyway.

  When I swung the apartment door open, my jaw dropped to the floor. She was stunning and definitely did not look 18. She wore a tight little blue skirt and a low cut red t-shirt. Her breasts were too large to avoid looking at, and they swayed with every small shift of her body. Her long, red hair curled slightly at the end and she had a full face of makeup. Her bright, red lips were stretched into a full smile as she laid her blue eyes on me.

  “Are you Brent?” I nodded and let her in. “This’ll be easy,” I heard her mumble underneath her breath. I was slightly offended and also slightly eased by her comment. She carried in two bags with her. One was a backpack with one strap hanging loose down the middle of her back. The other one was a big, sports duffle bag. “Where can I set these?”

  “I guess in the bedroom,” I said, feeling strange as the words left my mouth. She headed toward Jason’s at first, and before I could stop her she realized it was her brother’s.

  “Oops,” she said with a giggle. She eyed me up and down and smiled again. Her hair bounced as she walked. “You’re kinda shy, hm?”

  “Not usually,” I said defensively. “To be honest I feel weird about all of this.”

  “Crossdressing?” she asked.

  “That and…” my eyes traveled from her full breasts down the length of her tight but curvy body.

  “Oh. That I’m young? Don’t worry, I won’t rape you,” she teased. She winked at me and then found my bedroom. “Nice. You keep it neater than my brother.” I watched her ass shake as she moved and couldn’t believe she was about to feminize me.

  “Well?” she asked. “Are you coming?”

  I followed her into the room and then slowly closed the door.

  Chapter 3

  Nina laid her bags on my bed and started digging through them. “Jason said this was for a job interview of some sort?”

  “That’s correct,” I said, trying to stay as professional and reserved as possible, despite the fact that my cock was getting harder by the second.

  “What kind of job wants you to dress in drag?” she asked.

  “Um. They don’t necessarily want me to.” She turned toward me, her red hair flipping behind her back.

  “Then why are you?”

  “It’s hard to explain.” I knew it wasn’t hard, but she was a woman and I didn’t want to insult her. Thankfully, she shrugged it off and returned to digging through her bags.

  “I brought a pencil skirt. We look like we could be the same size, but I can make adjustments if necessary. Then I also brought a few different colored blouses, because I wasn’t sure what your skin tone would look like.”

  “What does that have to do with anything?”

  “Just trust me,” she said with a smile. “I also brought some lingerie because I wasn’t sure how far you needed to go with this…um…costume. Oh! and some heels!” She pulled out a tall pair of black heels and threw them on top of the skirt.

  Lingerie? Panties? Heels? How far was I really willing to go to get into this interview? “Thanks,” I said. I felt my heart pounding at the thought of having to put any of those things on.

  “I can leave the room if you want. Or,” she said, “I could stay and help you in case you get stuck on something.” She giggled again. “Or stuck in something.”

  I felt my cheeks redden as she laughed. I already felt humiliated and I hadn’t even put the skirt on yet. Despite my self-inflicted anxiety, my cock was hard as a rock. I was grateful for its small size so that Nina wouldn’t notice. But if I stripped in front of her, she’d have to see it. For that reason alone, I wanted to kick her out of the room, but I knew I would need help with a few things. Part of me wanted her to be there to guide me and take the edge off.

  “I guess you could stay,” I said nervously. Her eyes narrowed as she smiled.

  “Excellent!” She clapped her hands together and then pointed her finger at me. “Now, strip.”

  I reached for my shirt and slid it slowly above my head. Then I unfastened my shorts and slid them to my ankles. Even though I was only in my boxers, Nina still couldn’t tell that my dick was hard. I turned around to remove my boxers and she started to laugh.

  “You think I care about your dick? Come on, Brent. You can turn around.”

  “No. I can’t,” I replied.

  “Why? You hard or something?” I bowed my head in shame, but didn’t respond. “Oh my god! You are?” She burst into a fit of laughter and my cheeks flushed again.

  “Well, it’s nothing I haven’t seen before,” she said after calming herself down. “Come on. Don’t be shy.”

  I took a deep breath and turned around. Her eyes widened and her mouth fell open. “Ok. I haven’t seen that before.” She started laughing again.

  “What?”

  “You’re just…really small,” she teased.

  “What would you know? You’re just a kid.”

  “I’m 18 and I’ve had my fair share of sex. Usually with other girls, though.”

  This time, my eyes widened. “Really?” Of course, her mentioning lesbian sex only turned me on more. But I knew I couldn’t do anything sexual with her. She was my roommate’s little sister and it would be totally irresponsible of me.

  Not that she wanted me, anyway.

  “Just get over here, so I can dress you,” she said. I walked toward her nervously, with a hard, but small cock between my legs. “Here are some panties,” she said.

  She held out a pair of red lace panties with a butterfly design on the back. “I don’t know if I can wear these,” I admitted. She scoffed and shoved them at my chest.

  “Do you want to do this or not?”

  I gulped and nodded. Then I took the panties and slid my legs through them. It felt strange to push a pair of hairy legs through this delicate, soft fabric. I slid it up to my hips until it cupped my cock and then I fell into a state of bliss.

  Why does this feel so good? I was filled with panic at the thought that I was enjoying wearing women’s panties. I tried to shove the strange feelings down as far as they would go, but they were persistent.

  “Now this,” she said. “Do you know how to hook one of these?” Nina held out a matching red bra. It had two small cups that were heavily padded. I shook my head. I’d unhooked a bra before but it took what felt like hours.

  “Hold out your arms,” she directed. I extended my slender arms forward and she
slid the bra straps up my shoulders. Then she walked around behind me and hooked it. “You have a really cute butt, actually. Did you know that?”

  I shook my head and blushed. I couldn’t believe she was checking out my ass while it was covered in lacy panties. “Thanks,” I replied.

  “No, really. You aren’t just going to be able to pass as a woman. You’ll pass for a hot woman,” she said. I blushed again and lowered my head. Why does this feel like a compliment I want to receive?

  She walked back toward the pile of clothes and picked up the black pencil skirt. She spread open the waist and lowered herself to the floor. As she crouched down, I could see down her shirt and I noticed she was wearing a white lace bra that looked similar to my red one. I felt so conflicted. I felt like bonding with her over bras as much as I felt like fucking her hot little ass.

  What’s wrong with me? Why does this feel more exciting than it should? I gulped again and stepped into the pencil skirt. She slid it up and fastened it. It hugged my hips perfectly, and I had no idea I even had hips. This is insane. It feels too good, too right. I wasn’t sure how much longer I could stand feeling so comfortable in my own body.

  “Now. Here’s the fun part,” she said. Little did Nina know, I was already having more fun than I was comfortable with. “Pick a blouse.” She spread out five different shirts, all made of the same silky material but in different colors and with different sleeves. I gravitated toward the yellow one, but I was desperate to pick something I wouldn’t like. So I reached for the blue.

  The blouse had strappy design in the back that I couldn’t quite figure out. Nina giggled and then helped me secure it to my torso. It was incredibly uncomfortable and I was happy about that. But I couldn’t help but wonder how good it might feel to wear the yellow.

  “You know,” she said, stepping back and looking over my body. “I’d love to see you in this yellow blouse.” She picked it up and held it in front of her. Fuck. My thoughts exactly.